On the surface this seems reasonable. Give $50k gift to your local wildlife sancturary for example, and get invited to the annual fundraising meal.
Looks like the big loopholes involve things like 501(c)(4)s
Without spending too long trying to workout the loopholes, it seems the larger problem is with the definition of a charity in the first place?
Any income the government doesn't collect is made up for by the middle and lower class and/or more debt which increases inflation, which is mainly a middle and lower class burden.
For a guy who claims everyone should pay their fair share, he sure takes advantage of a lot of loopholes which he probably helped pay to have written.
He's an OG corporate raider and should be thought of as such, rather than a benevolent capitalist.